Whenever I see someone I'm interested in I always make sure I go and talk to them. That's as far as I've ever gotten.
The way I see this working is as follows:
- somebody catches my eye
- I go over and talk to them
- we get along well, stuff develops in pretty much the same way as if I had just met a new platonic friend
- ???
- We start holding hands. I've watched enough films to see that it pretty much escalates by itself from there.
The problem is that whenever I've done this, they were either cool but didn't show much of an interest in me, or their personality didn't resonate too deeply with mine which was a shame because I still thought they were gorgeous.
Now I'm not looking for somebody to spend the rest of my life with. Because that will take a lot of meeting people. But I am in the mood to experiment with intimate relationships, and now. Part of me wonders whether it's even worth it if they don't share my sense of humour. But another part of me thinks the steps above might be constraining me to only one type of relationship, those of the lifelong sort, which is why it's taking so long.
As you can see at step 4 there is clearly a gap between talking with them and holding hands that I don't know how to cross, which I'd currently do by explicitly asking can we hold hands. I wonder if the thing I'm missing is also the thing that would progress things to the physical without the person being your soulmate. When you go to parties you see drunk people breaking the touch barrier together without talking. What's the cue for that to happen? Should touch ever be the thing that advances a relationship with someone? How does that work? How do you make sure it's mutual? Or is the way to go really to wait until I meet someone I get along with so well that something clicks?
I doubt you're going to love the answer but it's basically "you just know."
It super depends on the person, the moment and the vibe. If it's been a date or two, maybe we'll be talking, turn face to face, the conversation fades, we're looking at each other and we both know we're gonna kiss, so we do. If we're all dancing, maybe you lock eyes and kind of slide into each other. Maybe you're at a party and jokes lead to childish bumping with your shoulder on the couch or whatever and you see how they respond.
If I had to boil it down for non drunk dancy events (those are just raw physical chemistry) as simple as I can it'd be something like (also, I'm just assuming genders etc, adjust as necessary):
Is she laughing at your jokes? Is she actively engaging in the conversation or just being polite while you talk at her?
Sounds dumb but is she playing with her hair? Looking into your eyes? Leaning in?
If this is all fairly new to you, then I'd play it safe and at some point in the conversation find something you both enjoy and could do together (maybe you like the same terrible dive bar, maybe there's a nice walk nearby, maybe somewhere fun for tapas) and then later on, when you think things have clicked, say something like "it's been amazing meeting you, but I really shouldn't abandon my friend Bill, even if you are way funnier and probably better looking. But maybe next week, can I buy you a drink at that dive bar/walk/tapas?"
Be prepared for rejection. It happens. It's not the end of the world, though you might feel it is at the time.